Pyridine → 3-Acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

HRID 379723노트

반응식

HRID 379723 반응식
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CC=CC=1.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl>[C:31]([NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[C:17](=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:33])[CH3:32]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 183678333-Amino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

생성물 1

HCID 183680413-Acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole수율 54%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-amino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole (300 mg, 0.88 mmol; example 1, step 2) in a mixture of dichloromethane (10 ml) and pyridine (0.08 ml, 0.96 mmol) was added acetyl chloride (0.07 ml, 0.96 mmol). After stirring for 4 h, the mixture was partitioned between 10% aqueous citric acid (50 ml) and diethyl ether (100 ml). The organic extract was washed consecutively with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml). After drying (MgSO4) and removal of solvent, the crude product was purified by flash chromatography eluting with ethyl acetate/hexane (1:1) to afford 183 mg (54%) of the titled compound as a yellow oil.

후처리

  1. customthe mixture was partitioned between 10% aqueous citric acid (50 ml) and diethyl ether (100 ml)
  2. extractionThe organic extract
  3. washwas washed consecutively with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml)
  4. customAfter drying
  5. custom(MgSO4) and removal of solvent
  6. customthe crude product was purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1:1)

출처 및 근거

ORD 기록
ord-2eedbdddd43344a7a0cec60b0c1f8e49
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300363B1

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